Shifting From Saving to Spending in Retirement – Richard Sheffield

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It turns out that one of the hardest habits to break in retirement isn’t work — it’s saving. Richard Sheffield joins us to share his deeply personal and sometimes humorous story of transitioning from a performance-driven corporate career to a more intentional and enjoyable life in retirement. A former executive at UPS, and author of Spend Your Damn Retirement Money!: Beat the Spending Fear to Find Your Dream Retirement, Richard opens up about his struggle to shift from a lifelong saver’s mindset to embracing enjoying the money he worked so hard to accumulate.

He discusses how outdated retirement plans, old success signals, and societal expectations can lead us astray, even long after we’ve walked away from work. But through self-reflection, rewriting his financial plan, and reconnecting with what brings him joy, Richard found the freedom to spend boldly, live fully, and say yes more often.

You’ll discover:

• Why many retirement plans need to be reviewed periodically – and sometimes reworked
• The emotional blocks that prevent smart people from moving from accumulating to spending
• Why your intentional spending matters more in retirement
• The surprising benefits of getting creative with how you spend
• Why it can be wise to give now, not just later

Richard Sheffield joins us from Miami.

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Bio

Richard Sheffield is a former executive and writer who shares thoughtful essays on retirement, identity, and personal reinvention. After a long career in the corporate world, Richard turned to writing as a way to make sense of his experience — and to help others navigate their own journeys into retirement. He’s a popular contributor on Medium, where his honest takes on life after work resonate with thousands of readers.

Now fully embracing a bigger, bolder, and more intentional approach to life, Richard writes about finding meaning beyond metrics and spending in ways that spark joy.

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For More on Richard Sheffield

Richard Sheffield on Medium

Spend Your Damn Retirement Money!: Beat the Spending Fear to Find Your Dream Retirement

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Podcast Episodes You May Like

How to Retire – Christine Benz

Unretired – Mark S. Walton

Your Next Years Your Best Years – Harry Agress, MD

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About The Retirement Wisdom Podcast

There are many podcasts on retirement, often hosted by financial advisors with their own financial motives, that cover the money side of the street. This podcast is different. You’ll get smarter about the investment decisions you’ll make about the most important asset you’ll have in retirement: your time.

About Retirement Wisdom

I help people who are retiring, but aren’t quite done yet, discover what’s next and build their custom version of their next life. A meaningful retirement doesn’t just happen by accident.

Schedule a call today to discuss how the Designing Your Life process created by Bill Burnett & Dave Evans can help you make your life in retirement a great one — on your own terms.

About Your Podcast Host

Joe Casey is an executive coach who helps people design their next life after their primary career and create their version of The Multipurpose Retirement.™ He created his own next chapter after a 26-year career at Merrill Lynch, where he was Senior Vice President and Head of HR for Global Markets & Investment Banking.

Joe has earned Master’s degrees from the University of Southern California in Gerontology (at age 60), the University of Pennsylvania, and Middlesex University (UK), a BA in Ps